RU2014136983A - SYNTHESIS AND NEW SALT FORMS (R) -5 - ((E) -2-pyrrolidin-3-ylvinyl) pyrimidine - Google Patents

SYNTHESIS AND NEW SALT FORMS (R) -5 - ((E) -2-pyrrolidin-3-ylvinyl) pyrimidine Download PDF

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RU2014136983A
RU2014136983A RU2014136983A RU2014136983A RU2014136983A RU 2014136983 A RU2014136983 A RU 2014136983A RU 2014136983 A RU2014136983 A RU 2014136983A RU 2014136983 A RU2014136983 A RU 2014136983A RU 2014136983 A RU2014136983 A RU 2014136983A
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pyrrolidin
pyrimidine
constipation
ylvinyl
treatment
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Сриниваса Рао АКИРЕДДИ
Балвиндер Сингх БХАТТИ
Тимоти Дж. Катбертсон
Гари Морис Далл
Крэйг Харрисон Миллер
Мл. Джозеф Пайк МИТЧЕНЕР
Хулио А. Муньос
Питер Альберт Оттен
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Таргасепт, Инк.
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    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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    • C07D207/06—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
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Abstract

1. Кристаллическая соль присоединения кислоты (R)-5-((E)-2-пирролидин-3-илвинил)пиримидина, в которой кислоту выбирают из метансульфоновой, малеиновой, фумаровой, лимонной, оротовой, 10-камфорсульфоновой и фенцифоса, для применения при лечении запора.2. Соль присоединения кислоты по п. 1, в которой кислота является лимонной, оротовой или малеиновой.3. Кристаллическая форма моноцитрата (R)-5-((E)-2-пирролидин-3-илвинил)пиримидина, представляющая собой полиморфную форму II моноцитрата (R)-5-((E)-2-пирролидин-3-илвинил)пиримидина, которая характеризуется диаграммой порошковой рентгеновской дифрактометрии, включающей по меньшей мере один из следующих пиков:для применения при лечении запора.4. Аморфная форма моноцитрата (R)-5-((E)-2-пирролидин-3-илвинил)пиримидина, в которой диаграмма XRPD соответствует приведенной на фиг.1, для применения при лечении запора.5. Полиморфная форма II моноцитрата (R)-5-((E)-2-пирролидин-3-илвинил)пиримидина, в которой диаграмма XRPD соответствует приведенной на фиг.3, для применения при лечении запора.6. Полиморфная форма III моноцитрата (R)-5-((E)-2-пирролидин-3-илвинил)пиримидина, которая характеризуется диаграммой порошковой рентгеновской дифрактометрии, включающей по меньшей мере один из следующих пиков:для применения при лечении запора.7. Полиморфная форма III моноцитрата (R)-5-((E)-2-пирролидин-3-илвинил)пиримидина, в которой диаграмма XRPDсоответствует приведенной на фиг.4, для применения при лечении запора.8. Полиморфная форма IV моноцитрата (R)-5-((E)-2-пирролидин-3-илвинил)пиримидина, которая характеризуется диаграммой порошковой рентгеновской дифрактометрии, включающей по меньшей мере один из следующих пиков:для применения при лечении запора.9. Полиморфная форма IV моноцитрата (R)-5-((E)-2-пирролидин-3-илвинил)пир1. The crystalline acid addition salt of (R) -5 - ((E) -2-pyrrolidin-3-ylvinyl) pyrimidine, in which the acid is selected from methanesulfonic, maleic, fumaric, citric, orotic, 10-camphorsulfonic and phenciphos, for use in the treatment of constipation. 2. The acid addition salt of claim 1, wherein the acid is citric, orotic, or maleic. The crystalline form of (R) -5 - ((E) -2-pyrrolidin-3-ylvinyl) pyrimidine monocytrate, which is the polymorphic form of monocytrate II (R) -5 - ((E) -2-pyrrolidin-3-ylvinyl) pyrimidine polymorph , which is characterized by a powder X-ray diffractometry diagram including at least one of the following peaks: for use in the treatment of constipation. 4. An amorphous form of (R) -5 - ((E) -2-pyrrolidin-3-yl-vinyl) -pyrimidine monocytrate in which the XRPD diagram corresponds to that shown in Fig. 1 for use in the treatment of constipation. 5. Polymorphic form II of monocytrate (R) -5 - ((E) -2-pyrrolidin-3-ylvinyl) pyrimidine, in which the XRPD diagram corresponds to that shown in figure 3, for use in the treatment of constipation. 6. The polymorphic form III of monocytrate (R) -5 - ((E) -2-pyrrolidin-3-ylvinyl) pyrimidine, which is characterized by a powder X-ray diffractometry diagram comprising at least one of the following peaks: for use in the treatment of constipation. 7. The polymorphic form III of monocytrate (R) -5 - ((E) -2-pyrrolidin-3-ylvinyl) pyrimidine, in which the XRPD diagram corresponds to that shown in figure 4, for use in the treatment of constipation. 8. The polymorphic form IV of monocytrate (R) -5 - ((E) -2-pyrrolidin-3-ylvinyl) pyrimidine, which is characterized by a powder X-ray diffractometry diagram comprising at least one of the following peaks: for use in the treatment of constipation. 9. Polymorphic form IV of monocytrate (R) -5 - ((E) -2-pyrrolidin-3-yl vinyl) pyr

Claims (18)

1. Кристаллическая соль присоединения кислоты (R)-5-((E)-2-пирролидин-3-илвинил)пиримидина, в которой кислоту выбирают из метансульфоновой, малеиновой, фумаровой, лимонной, оротовой, 10-камфорсульфоновой и фенцифоса, для применения при лечении запора.1. The crystalline acid addition salt of (R) -5 - ((E) -2-pyrrolidin-3-ylvinyl) pyrimidine, in which the acid is selected from methanesulfonic, maleic, fumaric, citric, orotic, 10-camphorsulfonic and phenciphos, for use in the treatment of constipation. 2. Соль присоединения кислоты по п. 1, в которой кислота является лимонной, оротовой или малеиновой.2. The acid addition salt of claim 1, wherein the acid is citric, orotic, or maleic. 3. Кристаллическая форма моноцитрата (R)-5-((E)-2-пирролидин-3-илвинил)пиримидина, представляющая собой полиморфную форму II моноцитрата (R)-5-((E)-2-пирролидин-3-илвинил)пиримидина, которая характеризуется диаграммой порошковой рентгеновской дифрактометрии, включающей по меньшей мере один из следующих пиков:3. The crystalline form of monocytrate (R) -5 - ((E) -2-pyrrolidin-3-ylvinyl) pyrimidine, which is the polymorphic form II of monocytrate (R) -5 - ((E) -2-pyrrolidin-3-ylvinyl ) pyrimidine, which is characterized by a powder X-ray diffractometry diagram comprising at least one of the following peaks: 2θ2θ   11,0211.02   20,0120.01   22,0622.06   24,6624.66   32,1332.13   33,3533.35   34,6134.61   35,9635.96   38,6538.65   40,2340,23  
для применения при лечении запора.for use in the treatment of constipation. 4. Аморфная форма моноцитрата (R)-5-((E)-2-пирролидин-3-илвинил)пиримидина, в которой диаграмма XRPD соответствует приведенной на фиг.1, для применения при лечении запора.4. An amorphous form of (R) -5 - ((E) -2-pyrrolidin-3-yl-vinyl) -pyrimidine monocytrate in which the XRPD diagram corresponds to that shown in FIG. 1 for use in the treatment of constipation. 5. Полиморфная форма II моноцитрата (R)-5-((E)-2-пирролидин-3-илвинил)пиримидина, в которой диаграмма XRPD соответствует приведенной на фиг.3, для применения при лечении запора.5. Polymorphic form II of monocytrate (R) -5 - ((E) -2-pyrrolidin-3-ylvinyl) pyrimidine, in which the XRPD diagram corresponds to that shown in figure 3, for use in the treatment of constipation. 6. Полиморфная форма III моноцитрата (R)-5-((E)-2-пирролидин-3-илвинил)пиримидина, которая характеризуется диаграммой порошковой рентгеновской дифрактометрии, включающей по меньшей мере один из следующих пиков:6. Polymorphic form III of monocytrate (R) -5 - ((E) -2-pyrrolidin-3-ylvinyl) pyrimidine, which is characterized by a powder X-ray diffractometry diagram comprising at least one of the following peaks: 2θ2θ   9,439.43   12,2412.24   16,2416.24   18,3818.38   19,1819.18   19,4819.48   21,5221.52   22,8922.89   23,0823.08   24,2824.28   30,7730.77   31,2731.27   32,3632.36   33,0933.09   34,8634.86   37,2637.26   37,6337.63   39,4739.47  
для применения при лечении запора.for use in the treatment of constipation. 7. Полиморфная форма III моноцитрата (R)-5-((E)-2-пирролидин-3-илвинил)пиримидина, в которой диаграмма XRPD 7. Polymorphic form III of monocytrate (R) -5 - ((E) -2-pyrrolidin-3-ylvinyl) pyrimidine in which the XRPD diagram соответствует приведенной на фиг.4, для применения при лечении запора.corresponds to that shown in figure 4, for use in the treatment of constipation. 8. Полиморфная форма IV моноцитрата (R)-5-((E)-2-пирролидин-3-илвинил)пиримидина, которая характеризуется диаграммой порошковой рентгеновской дифрактометрии, включающей по меньшей мере один из следующих пиков:8. Polymorphic form IV of monocytrate (R) -5 - ((E) -2-pyrrolidin-3-ylvinyl) pyrimidine, which is characterized by a powder X-ray diffractometry diagram comprising at least one of the following peaks: 2θ2θ   5,055.05   10,8110.81   14,0614.06   15,2015,20   17,4317.43   23,4723.47   24,2124.21   25,5225.52   26,9526.95  
для применения при лечении запора.for use in the treatment of constipation. 9. Полиморфная форма IV моноцитрата (R)-5-((E)-2-пирролидин-3-илвинил)пиримидина, в которой диаграмма XRPD соответствует приведенной на фиг.5, для применения при лечении запора.9. Polymorphic form IV of monocytrate (R) -5 - ((E) -2-pyrrolidin-3-ylvinyl) pyrimidine, in which the XRPD diagram corresponds to that shown in figure 5, for use in the treatment of constipation. 10. Кристаллическая форма монооротата (R)-5-((E)-2-пирролидин-3-илвинил)пиримидина, представляющая собой полиморфную форму монооротата (R)-5-((E)-2-пирролидин-3-илвинил)пиримидина, которая характеризуется диаграммой порошковой рентгеновской дифрактометрии, включающей по меньшей мере один из следующих пиков:10. The crystalline form of (R) -5 - ((E) -2-pyrrolidin-3-yl-vinyl) pyrimidine monorotate, which is the polymorphic form of (R) -5 - ((E) -2-pyrrolidin-3-yl-vinyl mono-rotate) pyrimidine, which is characterized by a powder X-ray diffractometry diagram including at least one of the following peaks: 2θ2θ  
2,552,55   6,546.54   8,668.66   13,2613.26   14,5614.56   15,9815.98   17,4717.47   18,5318.53   19,3019.30   20,2620.26   21,0521.05   22,0222.02   23,1423.14   24,3224.32   25,5625.56   26,8726.87   27,8427.84   28,7628.76   29,5329.53  
для применения при лечении запора.for use in the treatment of constipation. 11. Полиморфная форма монооротата (R)-5-((E)-2-пирролидин-3-илвинил)пиримидина, в которой диаграмма XRPD соответствует приведенной на фиг.6, для применения при лечении запора.11. The polymorphic form of the monorotate (R) -5 - ((E) -2-pyrrolidin-3-ylvinyl) pyrimidine, in which the XRPD diagram corresponds to that shown in Fig.6, for use in the treatment of constipation. 12. Кристаллическая форма мономалеата (R)-5-((E)-2-пирролидин-3-илвинил)пиримидина, представляющая собой полиморфную форму I мономалеата (R)-5-((E)-2-пирролидин-3-илвинил)пиримидина, которая характеризуется диаграммой порошковой рентгеновской дифрактометрии, включающей по меньшей мере один из следующих пиков:12. The crystalline form of (R) -5 - ((E) -2-pyrrolidin-3-ylvinyl) pyrimidine monomaleate, which is the polymorphic form of (R) -5 - ((E) -2-pyrrolidin-3-ylvinyl monomaleate ) pyrimidine, which is characterized by a powder X-ray diffractometry diagram comprising at least one of the following peaks: 2θ2θ   12,8112.81   16,0916.09  
18,0018.00   19,0719.07   24,4924.49   26,4026.40   26,0426.04   27,8827.88  
для применения при лечении запора.for use in the treatment of constipation. 13. Полиморфная форма I мономалеата (R)-5-((E)-2-пирролидин-3-илвинил)пиримидина, в которой диаграмма XRPD соответствует приведенной на фиг.7, для применения при лечении запора.13. Polymorphic form I of the (R) -5 - ((E) -2-pyrrolidin-3-ylvinyl) pyrimidine monomaleate, in which the XRPD diagram corresponds to that shown in Fig. 7, for use in the treatment of constipation. 14. Полиморфная форма II мономалеата (R)-5-((E)-2-пирролидин-3-илвинил)пиримидина, которая характеризуется диаграммой порошковой рентгеновской дифрактометрии, включающей по меньшей мере один из следующих пиков:14. Polymorphic form II of the (R) -5 - ((E) -2-pyrrolidin-3-ylvinyl) pyrimidine monomaleate, which is characterized by a powder X-ray diffractometry diagram including at least one of the following peaks: 2θ2θ   4,314.31   16,5616.56   18,2918.29   18,7818.78   19,6419.64   20,2720.27   21,0221.02   21,4621.46   21,9021.90   22,4322.43   22,8622.86   25,4025.40   25,7325.73   26,1526.15   26,5626.56   27,4027.40   28,5928.59   29,5729.57  
для применения при лечении запора.for use in the treatment of constipation. 15. Полиморфная форма II мономалеата (R)-5-((E)-2-пирролидин-3-илвинил)пиримидина, в которой диаграмма XRPD соответствует приведенной на фиг.8, для применения при лечении запора.15. Polymorphic form II of the (R) -5 - ((E) -2-pyrrolidin-3-ylvinyl) pyrimidine monomaleate, in which the XRPD diagram corresponds to that shown in Fig. 8, for use in the treatment of constipation. 16. Фармацевтическая композиция для применения при лечении запора, включающая эффективное количество соединения по любому из пп. 1-15 и один или более фармацевтически приемлемых носителей, разбавителей или эксципиентов.16. A pharmaceutical composition for use in the treatment of constipation, comprising an effective amount of a compound according to any one of claims. 1-15 and one or more pharmaceutically acceptable carriers, diluents or excipients. 17. Способ лечения запора, включающий введение соединения по любому из пп. 1-15.17. A method of treating constipation, comprising administering a compound according to any one of paragraphs. 1-15. 18. Применение соединения по любому из пп. 1-15 для изготовления лекарственного средства для лечения запора. 18. The use of compounds according to any one of paragraphs. 1-15 for the manufacture of a medicament for the treatment of constipation.
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